Sulfuric Acid → 11beta-Fluoro-17beta-hydroxy-7alpha-methylestr-4-en-3-one

HRID 855480Notes

Reaction equation

HRID 855480 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1.S(=O)(=O)(O)O>O1CCCC1>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[OH:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 10193144HCID 10193144, compound

Product 1

HCID 990463811beta-Fluoro-17beta-hydroxy-7alpha-methylestr-4-en-3-oneYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 8.7 g of 11β-fluoro-7α-methyl-estr-4-ene-3,17-dione in 148 ml of tetrahydrofuran was mixed drop by drop at 0° C. with 29.5 ml of 1 M lithium aluminium tri-tert-butoxyhydride in tetrahydrofuran and stirred for 5.5 hours at 0° C. Then, dilute sulfuric acid was added at 0° C., and the reaction solution was added to ice water, extracted three times with ethyl acetate, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 5.8 g 11β-fluoro-17β-hydroxy-7α-methylestr-4-en-3-one with a melting point of 143-144° C. was obtained. [α]D=+89.9° (CHCl3).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-3c0a9eb89a834d7095391db5b3a93e59
Source dataset
uspto-grants-2007_08
Patent number
US07262023B2

Reaction notes

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